Calix[6]tris(thio)ureas: heteroditopic receptors for the cooperative binding of organic ion pairs.
Identifieur interne : 000258 ( PubMed/Checkpoint ); précédent : 000257; suivant : 000259Calix[6]tris(thio)ureas: heteroditopic receptors for the cooperative binding of organic ion pairs.
Auteurs : Mélanie Hamon [France] ; Mickaël Ménand ; Stéphane Le Gac ; Michel Luhmer ; Vincent Dalla ; Ivan JabinSource :
- The Journal of organic chemistry [ 1520-6904 ] ; 2008.
English descriptors
- KwdEn :
- Binding Sites, Calixarenes (chemical synthesis), Calixarenes (chemistry), Ions (chemistry), Magnetic Resonance Spectroscopy (methods), Magnetic Resonance Spectroscopy (standards), Molecular Conformation, Phenols (chemical synthesis), Phenols (chemistry), Reference Standards, Stereoisomerism, Thiourea (analogs & derivatives), Thiourea (chemical synthesis), Thiourea (chemistry), Urea (analogs & derivatives), Urea (chemical synthesis), Urea (chemistry).
- MESH :
- chemical , analogs & derivatives : Thiourea, Urea.
- chemical , chemical synthesis : Calixarenes, Phenols, Thiourea, Urea.
- chemical , chemistry : Calixarenes, Ions, Phenols, Thiourea, Urea.
- methods : Magnetic Resonance Spectroscopy.
- standards : Magnetic Resonance Spectroscopy.
- Binding Sites, Molecular Conformation, Reference Standards, Stereoisomerism.
Abstract
The straightforward syntheses of C3v symmetrical calix[6]trisureas and -thiourea have been achieved. NMR studies have shown that these flexible compounds possess a major cone conformation. While these neutral hosts can strongly bind anions such as AcO(-) or HSO4(-) through induced fit processes, they can also behave as unique heteroditopic receptors for organic ion pairs with a remarkable positive cooperativity in the complexation process, the anion acting as an allosteric effector.
DOI: 10.1021/jo800712q
PubMed: 18712925
Affiliations:
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Ménand</name></author><author><name sortKey="Le Gac, Stephane" sort="Le Gac, Stephane" uniqKey="Le Gac S" first="Stéphane" last="Le Gac">Stéphane Le Gac</name></author><author><name sortKey="Luhmer, Michel" sort="Luhmer, Michel" uniqKey="Luhmer M" first="Michel" last="Luhmer">Michel Luhmer</name></author><author><name sortKey="Dalla, Vincent" sort="Dalla, Vincent" uniqKey="Dalla V" first="Vincent" last="Dalla">Vincent Dalla</name></author><author><name sortKey="Jabin, Ivan" sort="Jabin, Ivan" uniqKey="Jabin I" first="Ivan" last="Jabin">Ivan Jabin</name></author></titleStmt><publicationStmt><idno type="wicri:source">PubMed</idno><date when="2008">2008</date><idno type="RBID">pubmed:18712925</idno><idno type="pmid">18712925</idno><idno type="doi">10.1021/jo800712q</idno><idno type="wicri:Area/PubMed/Corpus">000251</idno><idno type="wicri:Area/PubMed/Curation">000251</idno><idno type="wicri:Area/PubMed/Checkpoint">000251</idno></publicationStmt><sourceDesc><biblStruct><analytic><title xml:lang="en">Calix[6]tris(thio)ureas: heteroditopic receptors for the cooperative binding of organic ion pairs.</title><author><name sortKey="Hamon, Melanie" sort="Hamon, Melanie" uniqKey="Hamon M" first="Mélanie" last="Hamon">Mélanie Hamon</name><affiliation wicri:level="4"><nlm:affiliation>URCOM, Université du Havre, FST, 25 rue Philippe Lebon, BP 540, 76058 Le Havre cedex, France.</nlm:affiliation><country xml:lang="fr">France</country><wicri:regionArea>URCOM, Université du Havre, FST, 25 rue Philippe Lebon, BP 540, 76058 Le Havre cedex</wicri:regionArea><placeName><region type="region" nuts="2">Région Normandie</region><region type="old region" nuts="2">Haute-Normandie</region><settlement type="city">Le Havre</settlement></placeName><orgName type="university">Université du Havre</orgName></affiliation></author><author><name sortKey="Menand, Mickael" sort="Menand, Mickael" uniqKey="Menand M" first="Mickaël" last="Ménand">Mickaël Ménand</name></author><author><name sortKey="Le Gac, 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(methods)</term><term>Magnetic Resonance Spectroscopy (standards)</term><term>Molecular Conformation</term><term>Phenols (chemical synthesis)</term><term>Phenols (chemistry)</term><term>Reference Standards</term><term>Stereoisomerism</term><term>Thiourea (analogs & derivatives)</term><term>Thiourea (chemical synthesis)</term><term>Thiourea (chemistry)</term><term>Urea (analogs & derivatives)</term><term>Urea (chemical synthesis)</term><term>Urea (chemistry)</term></keywords><keywords scheme="MESH" type="chemical" qualifier="analogs & derivatives" xml:lang="en"><term>Thiourea</term><term>Urea</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemical synthesis" xml:lang="en"><term>Calixarenes</term><term>Phenols</term><term>Thiourea</term><term>Urea</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Calixarenes</term><term>Ions</term><term>Phenols</term><term>Thiourea</term><term>Urea</term></keywords><keywords 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NMR studies have shown that these flexible compounds possess a major cone conformation. While these neutral hosts can strongly bind anions such as AcO(-) or HSO4(-) through induced fit processes, they can also behave as unique heteroditopic receptors for organic ion pairs with a remarkable positive cooperativity in the complexation process, the anion acting as an allosteric effector.</div></front></TEI><pubmed><MedlineCitation Status="MEDLINE" Owner="NLM"><PMID Version="1">18712925</PMID><DateCreated><Year>2008</Year><Month>9</Month><Day>16</Day></DateCreated><DateCompleted><Year>2008</Year><Month>11</Month><Day>14</Day></DateCompleted><DateRevised><Year>2013</Year><Month>11</Month><Day>21</Day></DateRevised><Article PubModel="Print-Electronic"><Journal><ISSN IssnType="Electronic">1520-6904</ISSN><JournalIssue CitedMedium="Internet"><Volume>73</Volume><Issue>18</Issue><PubDate><Year>2008</Year><Month>Sep</Month><Day>19</Day></PubDate></JournalIssue><Title>The Journal of organic chemistry</Title><ISOAbbreviation>J. Org. Chem.</ISOAbbreviation></Journal><ArticleTitle>Calix[6]tris(thio)ureas: heteroditopic receptors for the cooperative binding of organic ion pairs.</ArticleTitle><Pagination><MedlinePgn>7067-71</MedlinePgn></Pagination><ELocationID EIdType="doi" ValidYN="Y">10.1021/jo800712q</ELocationID><Abstract><AbstractText>The straightforward syntheses of C3v symmetrical calix[6]trisureas and -thiourea have been achieved. NMR studies have shown that these flexible compounds possess a major cone conformation. While these neutral hosts can strongly bind anions such as AcO(-) or HSO4(-) through induced fit processes, they can also behave as unique heteroditopic receptors for organic ion pairs with a remarkable positive cooperativity in the complexation process, the anion acting as an allosteric effector.</AbstractText></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Hamon</LastName><ForeName>Mélanie</ForeName><Initials>M</Initials><AffiliationInfo><Affiliation>URCOM, Université du Havre, FST, 25 rue Philippe Lebon, BP 540, 76058 Le Havre cedex, France.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Ménand</LastName><ForeName>Mickaël</ForeName><Initials>M</Initials></Author><Author ValidYN="Y"><LastName>Le Gac</LastName><ForeName>Stéphane</ForeName><Initials>S</Initials></Author><Author ValidYN="Y"><LastName>Luhmer</LastName><ForeName>Michel</ForeName><Initials>M</Initials></Author><Author ValidYN="Y"><LastName>Dalla</LastName><ForeName>Vincent</ForeName><Initials>V</Initials></Author><Author ValidYN="Y"><LastName>Jabin</LastName><ForeName>Ivan</ForeName><Initials>I</Initials></Author></AuthorList><Language>ENG</Language><PublicationTypeList><PublicationType UI="D016428">Journal Article</PublicationType><PublicationType UI="D013485">Research Support, Non-U.S. Gov't</PublicationType></PublicationTypeList><ArticleDate DateType="Electronic"><Year>2008</Year><Month>Aug</Month><Day>20</Day></ArticleDate></Article><MedlineJournalInfo><Country>United States</Country><MedlineTA>J Org Chem</MedlineTA><NlmUniqueID>2985193R</NlmUniqueID><ISSNLinking>0022-3263</ISSNLinking></MedlineJournalInfo><ChemicalList><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D007477">Ions</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D010636">Phenols</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="C476540">calix(6)arene</NameOfSubstance></Chemical><Chemical><RegistryNumber>130036-26-9</RegistryNumber><NameOfSubstance UI="D047250">Calixarenes</NameOfSubstance></Chemical><Chemical><RegistryNumber>8W8T17847W</RegistryNumber><NameOfSubstance UI="D014508">Urea</NameOfSubstance></Chemical><Chemical><RegistryNumber>GYV9AM2QAG</RegistryNumber><NameOfSubstance UI="D013890">Thiourea</NameOfSubstance></Chemical></ChemicalList><CitationSubset>IM</CitationSubset><MeshHeadingList><MeshHeading><DescriptorName UI="D001665" MajorTopicYN="N">Binding Sites</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D047250" MajorTopicYN="N">Calixarenes</DescriptorName><QualifierName UI="Q000138" MajorTopicYN="N">chemical synthesis</QualifierName><QualifierName UI="Q000737" MajorTopicYN="Y">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D007477" MajorTopicYN="N">Ions</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D009682" MajorTopicYN="N">Magnetic Resonance Spectroscopy</DescriptorName><QualifierName UI="Q000379" MajorTopicYN="N">methods</QualifierName><QualifierName UI="Q000592" MajorTopicYN="N">standards</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D008968" MajorTopicYN="N">Molecular Conformation</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D010636" MajorTopicYN="N">Phenols</DescriptorName><QualifierName UI="Q000138" MajorTopicYN="N">chemical synthesis</QualifierName><QualifierName UI="Q000737" MajorTopicYN="Y">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D012015" MajorTopicYN="N">Reference Standards</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D013237" MajorTopicYN="N">Stereoisomerism</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D013890" MajorTopicYN="N">Thiourea</DescriptorName><QualifierName UI="Q000031" MajorTopicYN="Y">analogs & derivatives</QualifierName><QualifierName UI="Q000138" MajorTopicYN="N">chemical synthesis</QualifierName><QualifierName UI="Q000737" MajorTopicYN="Y">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D014508" MajorTopicYN="N">Urea</DescriptorName><QualifierName UI="Q000031" MajorTopicYN="Y">analogs & derivatives</QualifierName><QualifierName UI="Q000138" MajorTopicYN="N">chemical synthesis</QualifierName><QualifierName UI="Q000737" MajorTopicYN="Y">chemistry</QualifierName></MeshHeading></MeshHeadingList></MedlineCitation><PubmedData><History><PubMedPubDate PubStatus="pubmed"><Year>2008</Year><Month>8</Month><Day>21</Day><Hour>9</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="medline"><Year>2008</Year><Month>11</Month><Day>15</Day><Hour>9</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="entrez"><Year>2008</Year><Month>8</Month><Day>21</Day><Hour>9</Hour><Minute>0</Minute></PubMedPubDate></History><PublicationStatus>ppublish</PublicationStatus><ArticleIdList><ArticleId IdType="pubmed">18712925</ArticleId><ArticleId IdType="doi">10.1021/jo800712q</ArticleId></ArticleIdList></PubmedData></pubmed><affiliations><list><country><li>France</li></country><region><li>Haute-Normandie</li><li>Région Normandie</li></region><settlement><li>Le Havre</li></settlement><orgName><li>Université du Havre</li></orgName></list><tree><noCountry><name sortKey="Dalla, Vincent" sort="Dalla, Vincent" uniqKey="Dalla V" first="Vincent" last="Dalla">Vincent Dalla</name><name sortKey="Jabin, Ivan" sort="Jabin, Ivan" uniqKey="Jabin I" first="Ivan" last="Jabin">Ivan Jabin</name><name sortKey="Le Gac, Stephane" sort="Le Gac, Stephane" uniqKey="Le Gac S" first="Stéphane" last="Le Gac">Stéphane Le Gac</name><name sortKey="Luhmer, Michel" sort="Luhmer, Michel" uniqKey="Luhmer M" first="Michel" last="Luhmer">Michel Luhmer</name><name sortKey="Menand, Mickael" sort="Menand, Mickael" uniqKey="Menand M" first="Mickaël" last="Ménand">Mickaël Ménand</name></noCountry><country name="France"><region name="Région Normandie"><name sortKey="Hamon, Melanie" sort="Hamon, Melanie" uniqKey="Hamon M" first="Mélanie" last="Hamon">Mélanie Hamon</name></region></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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